t-Butyldimethylsilyl ethers of sucrose

Abstract

The usefulness of the t-butyldimethylsilyl group as a blocking group in carbohydrate chemistry has been demonstrated and its selectivity towards primary hydroxyl groups, in the absence of imidazole, shown by preparation of derivatives of methyl α-D-glucopyranoside and sucrose. Methyl α-D-gluco-pyranoside was converted into methyl 6-O-t- butyldimethylsilyl-a-D-glucopyranoside in almost quantitative yield, and sucrose to 6,1?,6?-tri-O-t-butyldimethylsilylsucrose in good yield. In the presence of excess sucrose, a mixture of 6?-O-t- butyldimethylsilyl-, 6,6?-di-O-t-butyldimethylsilyl- and 6,1?,6?-tri-O- t-butyldimethylsilyl-sucroses was formed.